Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 days." They meet in a bar shortly after the bet is made.
When her brother decides to ditch for a couple weeks, Viola heads over to his elite boarding school, disguised as him, and proceeds to fall for one of his soccer teammates, and soon learns she's not the only one with romantic troubles.
Two things about Jane: she never says no to her friends (she's been a bridesmaid 27 times and selflessly plans friends' weddings), and she's in love with her boss, George, nurturing dreams of a lovely, romantic wedding of her own. She meets Kevin, a cynical writer who finds her attractive, and that same week her flirtatious younger sister Tess comes to town. Jane silently watches George fall for Tess, a manipulative pretender. Worse, Jane may be called upon to plan their wedding. Meanwhile, Kevin tries to get Jane's attention and has an idea that may advance his career. Can Jane uncork her feelings?Written by